We propose to explore and develop several recently discovered reaction sequences involving alpha, Beta-unsaturated ketones. By applying these reactions to steroid or steroid-like substrates we expect to generate novel and potentially useful modified steroids, as well as determining the scope and limitations of these synthetic tools. Our specific objectives in studying these reactions include: 1) The synthesis of various methyl substituted steroids by alkylation of the cross-conjugated dienolate bases derived from steroidal enones. 2) The synthesis and subsequent reaction of 2-alkoxy-1, 3-cyclohexadienes derived from steroidal enones. Photochemical rearrangement and oxidation of such substrates offers an attractive route to some vitamin D analogs. 3) The use of sequential Michael reactions involving cross- conjugated dienolate anions in the synthesis of bicyclo(2.2.2)octane derivatives of steroids. This alternative to Diels-Alder cyclization should provide a facile synthesis of the sesquiterpene seychellene.